CN103305231B - Liquid crystal composite containing difluorooxymethylene bridge polar monomer compound - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 127
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 81
- 239000000178 monomer Substances 0.000 title claims abstract description 25
- 239000002131 composite material Substances 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 230000004044 response Effects 0.000 abstract description 10
- 239000010409 thin film Substances 0.000 abstract description 6
- 238000012360 testing method Methods 0.000 description 33
- 239000000463 material Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000005388 borosilicate glass Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IGDOKHBQDKXLSE-UHFFFAOYSA-N 1,1'-biphenyl oxalonitrile Chemical compound N#CC#N.C1(=CC=CC=C1)C1=CC=CC=C1 IGDOKHBQDKXLSE-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- -1 fluorine cyanogen ester Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a liquid crystal composite containing a difluorooxymethylene bridge polar monomer compound. The liquid crystal composite comprises the following components in percentage by weight: 1%-40% of compounds shown in a general formula I, 1%-40% of compounds shown in a general formula II, 5%-70% of compounds shown in a general formula III, 1%-60% of compounds shown in a general formula IV, 0%-20% of compounds shown in a general formula V and 0%-20% of compounds shown in a general formula VI. The liquid crystal composite disclosed by the invention has the characteristics of high response speed, low driving voltage and high resistivity and voltage conservation rate, has the capability of improving the viewing angle of a liquid crystal display by heightening the pretilt angle of a liquid crystal in a display and is suitable for a fast-responsive TFT-LCD (Thin Film Transistor Liquid Crystal Display).
Description
Technical Field
The invention relates to a liquid crystal display material, in particular to a liquid crystal composition containing a difluoromethoxy bridge polar monomer compound.
Background
There are many liquid crystal display modes, but a mode for realizing display by utilizing a photoelectric effect of liquid crystal is widely used. The photoelectric effect actually means that the arrangement of liquid crystal molecules changes from one state to another upon application of electricity, thereby changing the photoelectric properties of the liquid crystal cell. The first liquid crystal display in the world appeared in the early seventies and was called TN mode liquid crystal display (Twisted Nematic). In eighties, an STN type liquid crystal display (Super Twisted Nematic) appeared, and meanwhile, a TFT liquid crystal display (Thin Film Transistor) technology was proposed. TFT is a abbreviation of thin film transistor ("TFT"), which is a technology for driving a liquid crystal material to display using a thin film transistor ("TFT").
Liquid crystal compounds containing end cyano groups are widely used in TN and STN liquid crystal display industries, such as monomer liquid crystal materials of biphenyl cyanogen, fluorine cyanogen ester, end alkene, diene, dicycline, tricycline and the like, the production process flow of the liquid crystal monomers is mature, and the liquid crystal monomers can be completely supplied in batches at home. However, researches show that the compounds containing terminal cyano groups are easy to introduce ionic impurities, have low voltage holding ratio VHR, high viscosity, slow response and poor chemical stability such as light, heat and the like, and the application of the compounds in TFT-LCDs is limited by the adverse factors. The ester liquid crystal has the characteristics of simple synthesis method, various types and wider phase change interval, but has the important defects of higher viscosity and poorer chemical stability, so that the dosage of the ester liquid crystal in a TFT-LCD formula is greatly reduced. Although the TFT-LCD also utilizes the principle of TN type electro-optic effect, the liquid crystal material for the TFT-LCD is different from the conventional liquid crystal material. Besides good physical and chemical stability and wide working temperature range, the liquid crystal material for TFT-LCD must also have the following characteristics:
(1) low viscosity to meet the need for fast response;
(2) high voltage holding ratio, which means that the liquid crystal material must have high resistivity, generally more than 1012 Ω · cm;
(3) a lower threshold voltage (Vth) to achieve low voltage driving and lower power consumption;
(4) optical anisotropy (Δ n) matched to TFT-LCD to eliminate rainbow effect and obtain large contrast and wide-angle visual field. The delta n value is generally in the range of 0.07-0.12, preferably about 0.08-0.1;
(5) different from TN and STN liquid crystal materials, the TFT liquid crystal material has high requirement on the chemical purity of monomers, and the bulk purity is over 99.9 percent. In addition, the kinds and amounts of various organic ions and inorganic ions need to be strictly controlled to achieve better practical effects and longer service life of the TFT-LCD.
As liquid crystal materials, it is first of all necessary to have good chemical and thermal stability and stability to electric fields and electromagnetic radiation. As a liquid crystal material for thin film transistor (TFT-LCD) technology, it is required to have not only the above stability, but also a wide nematic phase temperature range, a suitable birefringence anisotropy, a very high resistivity, a good uv resistance, a high charge retention rate, and a low vapor pressure.
Although the market for thin film transistor technology (TFT-LCD) applications is very large in recent years, the technology is mature, and meanwhile, due to the continuous progress of liquid crystal material technology, the requirements of people on display technology are continuously improved, especially in the aspects of realizing fast response, reducing driving voltage to reduce power consumption and the like.
Disclosure of Invention
The invention aims to provide a liquid crystal composition containing a difluoromethoxy bridge polar monomer compound, which is suitable for a TFT-LCD display and has high charge retention rate, low power consumption, low rotational viscosity and high response speed.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a liquid crystal composition containing a difluoromethoxy bridge polar monomer compound comprises 1-40% by mass of a compound shown in a general formula I, 1-40% by mass of a compound shown in a general formula II, 5-70% by mass of a compound shown in a general formula III, 1-60% by mass of a compound shown in a general formula IV, 0-20% by mass of a compound shown in a general formula V and 0-20% by mass of a compound shown in a general formula VI; and the sum of the mass percentages of the compounds shown in the general formulas I to VI in the liquid crystal composition is 100 percent, and in addition, 0 to 0.5 percent of optically active compounds with the sum of the mass percentages of the compounds shown in the general formulas I to VI in the mass percentage are added,
wherein,
R1、R3、R9、X6、X9is any one of the groups listed in the following (I) to (IV):
①：-H、-Cl、-F、-CN、-OCN、-OCF3、-CF3、-CHF2、-CH2F、-OCHF2、-SCN、-NCS、-SF5，
secondly, the step of: an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an alkenyloxy group having 2 to 15 carbon atoms,
③: one or more-CH groups of the above-mentioned group2Radicals not directly linked to the oxygen atom formed by substitution with-CH = CH-, -C.ident.C-, -COO-, -OOC-, cyclobutane, cyclopentane, -O-, -S-,
fourthly, the method comprises the following steps: a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine, or a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine;
R2、R4、R5、R6、R7、R8is one of-H, alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms, or one of groups formed by substituting one or more hydrogen in alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms by fluorine;
X1、X2、X3、X4、X5、X7、X8is one of-H or-F;
Z1、Z2、Z3、Z4、Z5is a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF = CF-;
is a single bond or one of the following groups:
a. b is any one of the values of 0, 1, 2 or 3, c is any one of the values of 1 or 2, and a + b + c is less than or equal to 5;
d. f is any value of 0, 1, 2 or 3, e is any value of 1 or 2, and d + e + f is less than or equal to 5;
g. h, i, j, k, l are any of the values 0, 1, 2 or 3.
Due to the adoption of the technical scheme, the technical progress of the invention is as follows:
the liquid crystal composition containing the difluoromethoxy bridge polar monomer compound has the advantages of quick response time, lower driving voltage, high resistivity and voltage holding ratio, low power consumption and low rotational viscosity, can also obviously improve the pretilt angle of a liquid crystal material in a liquid crystal display, is suitable for active matrix electro-optical elements and the liquid crystal display, and can be used for manufacturing a TFT-LCD with quick response and wide viewing angle.
The liquid crystal composition containing the difluoromethoxy bridge polar monomer compound still can show high resistivity after high temperature, and has excellent high-temperature and ultraviolet stability. In addition, the nematic liquid crystal composition of the present invention has low viscosity, fast response time, appropriate optical anisotropy and dielectric anisotropy.
Detailed Description
The present invention will be described in further detail with reference to examples.
The percentages in the specification are mass percentages; temperature in degrees Celsius (. degree. C.); the specific meanings and test conditions for the other symbols are as follows:
c.p. (DEG C) represents the clearing point of the liquid crystal; s → N represents the crystalline to nematic melting point (. degree. C.) of the liquid crystal; Δ n is optical anisotropy, no is the refractive index of ordinary light, ne is the refractive index of extraordinary light, and the test conditions are as follows: 589nm, 25 deg.C; Δ =dielectric anisotropy∥-⊥Wherein∥is the dielectric constant parallel to the molecular axis,⊥for the dielectric constant perpendicular to the molecular axis, the test conditions were: 25 ℃, 1KHz, HP4284A, 5.2 micron TN levo-box; tau is response time (ms), the test instrument is DMS-501, and the test conditions are as follows: 25 +/-0.5 ℃, a 4.0-micron TN left-handed cassette and a DMS-501 test instrument; v10Is the optical threshold voltage (V), V, of the liquid crystal90Is the saturation voltage value (v) of the liquid crystal, and the test conditions are as follows: 25 ℃ and 5.2 micron TN levorotatory box; ρ is resistivity (Ω · cm), test conditions are: 25 +/-2 ℃, and the testing instruments are a TOYOSR6517 high-impedance instrument and an LE-21 liquid electrode; gamma ray1As the rotational viscosity (mPas), the test conditions were: 25 plus or minus 0.5 ℃; the Pretilt angle is the Pretilt angle, the test instrument is tsukamur RETS-100, and a 20-micron parallel box; the UV post-test consists in placing a sample of the liquid-crystal mixture in a TN test cell with a pass intensity of 50mw/cm2Irradiating by a 365nm UV lamp for 100 seconds and then testing; the resistivity test after high temperature refers to that a sample containing the liquid crystal composition is put into a high borosilicate glass bottle, and is heated for 1 hour at the high temperature of 100 ℃ and then is recovered to the room temperature for testing; the test of voltage holding ratio after high temperature refers to the test containing the liquid crystal compositionPutting the sample into a high borosilicate glass bottle, continuously heating the sample for 1 hour at the high temperature of 100 ℃, then returning the temperature to the room temperature, and pouring the sample into a TN test box for testing.
The respective component compounds used in the following examples can be synthesized by a known method or obtained commercially. All the liquid crystal compounds meet the standard of electronic compounds through tests.
The invention relates to a liquid crystal composition containing a difluoromethoxy bridge polar monomer compound, which comprises a compound shown as a general formula I, a compound shown as a general formula II, a compound shown as a general formula III, a compound shown as a general formula IV, a compound shown as a general formula V and a compound shown as a general formula VI,
wherein,
R1、R3、R9、X6、X9is any one of the groups listed in the following (I) to (IV):
①：-H、-Cl、-F、-CN、-OCN、-OCF3、-CF3、-CHF2、-CH2F、-OCHF2、-SCN、-NCS、-SF5，
secondly, the step of: an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an alkenyloxy group having 2 to 15 carbon atoms,
③: one or more-CH groups of the above-mentioned group2Radicals not directly linked to the oxygen atom formed by substitution with-CH = CH-, -C.ident.C-, -COO-, -OOC-, cyclobutane, cyclopentane, -O-, -S-,
fourthly, the method comprises the following steps: a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine, or a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine;
R2、R4、R5、R6、R7、R8is one of-H, alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms, or one of groups formed by substituting one or more hydrogen in alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms by fluorine;
X1、X2、X3、X4、X5、X7、X8is one of-H or-F;
Z1、Z2、Z3、Z4、Z5is a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF = CF-;
is a single bond or one of the following groups:
a. b is any one of the values of 0, 1, 2 or 3, c is any one of the values of 1 or 2, and a + b + c is less than or equal to 5;
d. f is any value of 0, 1, 2 or 3, e is any value of 1 or 2, and d + e + f is less than or equal to 5;
g. h, i, j, k, l are any of the values 0, 1, 2 or 3.
When preparing the liquid crystal compound, 1-40% by mass of one or more compounds shown in the general formula I, 1-40% by mass of one or more compounds shown in the general formula II, 5-70% by mass of one or more compounds shown in the general formula III, 1-60% by mass of one or more compounds shown in the general formula IV, 0-20% by mass of one or more compounds shown in the general formula V and 0-20% by mass of one or more compounds shown in the general formula VI are mixed, and finally the sum of the mass percentages of the compounds shown in the general formulas I-VI in the liquid crystal composition containing the difluoromethoxy bridge type polar monomer compound is 100%; and an optically active compound which is the sum of the mass of the compounds represented by the general formulae I to VI and is added in an amount of 0 to 0.5% by mass.
The preferable proportion of the liquid crystal composition containing the difluoromethoxy bridge polar monomer compound is as follows: the content of the compound shown in the general formula I is 5-35% by mass, the content of the compound shown in the general formula II is 5-35% by mass, the content of the compound shown in the general formula III is 10-50% by mass, the content of the compound shown in the general formula IV is 5-60% by mass, the content of the compound shown in the general formula V is 0-10% by mass, and the content of the compound shown in the general formula VI is 0-10% by mass; the sum of the mass percentages of the compounds shown in the general formulas I to VI in the liquid crystal composition containing the difluoromethoxy bridge polar monomer compound is 100 percent; and an optically active compound which is the sum of the mass of the compounds represented by the general formulae I to VI and is added in an amount of 0 to 0.5% by mass.
In the liquid crystal composition containing the difluoromethoxy bridge polar monomer compound, the compound shown in the general formula I, the compound shown in the general formula II, the compound shown in the general formula III, the compound shown in the general formula IV, the compound shown in the general formula V and the compound shown in the general formula VI can be preferably selected from one or more compounds in the following formula, wherein (F) is one of-F or-H, the meanings represented by other symbols are the same as the meanings represented by the same symbols in the structural formula,
in the liquid crystal composition containing the difluoromethoxy bridge polar monomer compound, one or more of the compounds shown in the general formula I, the compounds shown in the general formula II, the compounds shown in the general formula III, the compounds shown in the general formula IV, the compounds shown in the general formula V and the compounds shown in the general formula VI are most preferably selected from the following compounds:
in the following examples 1 to 10, one or more compounds represented by general formula I, general formula II, general formula III, general formula IV, general formula V, and general formula VI are taken, and a liquid crystal composition containing a difluoromethoxy bridge polar monomer compound is prepared in proportion, and an optically active compound is further added. The prepared liquid crystal composition is filled between two substrates of the liquid crystal display for performance test.
The monomer structure, the amount (mass percent) of the specific compound and the performance parameter test results of the prepared liquid crystal composition are all shown in the table. Tables 1 to 10 correspond to examples 1 to 10.
TABLE 1 liquid crystal composition formulation of example 1 and its test performance parameters
Table 2 liquid crystal composition formulation of example 2 and its test performance parameters
Table 3 liquid crystal composition formulation of example 3 and its test performance parameters
Table 4 liquid crystal composition formulation of example 4 and its test performance parameters
TABLE 5 liquid crystal composition formulation of example 5 and its test performance parameters
TABLE 6 liquid crystal composition formulation of example 6 and its test performance parameters
TABLE 7 liquid crystal composition formulation of example 7 and its test performance parameters
TABLE 8 liquid crystal composition formulation of example 8 and its test performance parameters
TABLE 9 liquid crystal composition formulation of example 9 and its test performance parameters
TABLE 10 liquid crystal composition formulation of example 10 and its test performance parameters
From examples 1 to 10, it is clear that the liquid crystal compositions containing the difluoromethoxy bridge polar monomer compound all have large dielectric anisotropy of absolute value, high clearing point, and good low-temperature stability, and are very suitable for TFT-LCDs with low-voltage driving, fast response, and wide viewing angle.
Although the present invention only exemplifies specific materials and proportioning mass percentages of the above 10 examples, and tests the performance of the liquid crystal composition, the liquid crystal composition of the present invention can utilize the compounds represented by the general formulas I, II, III, IV, V, and VI and the preferred compounds of the general formulas I, II, III, IV, V, and VI to further develop and modify on the basis of the above examples, and can achieve the purpose of the present invention.
Claims (4)
1. A liquid crystal composition containing a difluoromethoxy bridge polar monomer compound is characterized in that: the composition comprises 1-40% by mass of a compound shown in a general formula I, 1-40% by mass of a compound shown in a general formula II, 5-70% by mass of a compound shown in a general formula III, 1-60% by mass of a compound shown in a general formula IV, 0-20% by mass of a compound shown in a general formula V and 4-20% by mass of a compound shown in a general formula VI; and the sum of the mass percentages of the compounds shown in the general formulas I to VI in the liquid crystal composition is 100 percent, and in addition, 0 to 0.5 percent of optically active compounds with the sum of the mass percentages of the compounds shown in the general formulas I to VI in the mass percentage are added,
wherein,
R1、R3、R9、X6、X9is any one of the groups listed in the following (I) to (IV):
①：-H、-F、-OCF3、-CF3、-CHF2、-CH2F、-OCHF2，
secondly, the step of: an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an alkenyloxy group having 2 to 15 carbon atoms,
③: one or more-CH groups of the above-mentioned group2Radicals not directly linked to the oxygen atom formed by-CH- ═ CH-, -COO-, -OOC-, cyclobutane, cyclopentane, -O-substitution,
fourthly, the method comprises the following steps: a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine, or a group formed by replacing one or more hydrogens in the group in the formula (iii) above with fluorine or chlorine;
R2、R4、R5、R6、R7、R8is one of-H, alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms, or one of groups formed by substituting one or more hydrogen in alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms and alkenyloxy with 3 to 8 carbon atoms by fluorine;
X1、X2、X5、X7、X8is one of-H or-F;
Z1、Z2、Z3、Z4、Z5is a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-one of (a);
is a single bond or one of the following groups:
a. b is any one of the values of 0, 1, 2 or 3, c is any one of the values of 1 or 2, and a + b + c is less than or equal to 5;
d. f is any value of 0, 1, 2 or 3, e is any value of 1 or 2, and d + e + f is less than or equal to 5;
g. h, i, j, k, l are any of the values 0, 1, 2 or 3.
2. The liquid crystal composition containing a difluoromethoxy bridge type polar monomer compound as claimed in claim 1, wherein: the content of the compound shown in the general formula I is 5-35% by mass, the content of the compound shown in the general formula II is 5-35% by mass, the content of the compound shown in the general formula III is 10-50% by mass, the content of the compound shown in the general formula IV is 5-60% by mass, the content of the compound shown in the general formula V is 0-10% by mass, the content of the compound shown in the general formula VI is 4-10% by mass, and the sum of the mass percentages of the compounds shown in the general formulas I-VI in the liquid crystal composition is 100%; and an optically active compound which is the sum of the mass of the compounds represented by the general formulae I to VI and is added in an amount of 0 to 0.5% by mass.
3. The liquid crystal composition containing a difluoromethoxy bridge type polar monomer compound according to any one of claims 1 or 2, wherein:
the compound shown in the general formula I is one or more of compounds shown in general formulas I-a-I-r,
the compound shown in the general formula II is one or more compounds shown in general formulas II-a-II-r,
the compound shown in the general formula III is one or more of compounds shown in general formulas III-a to III-i,
the compound shown in the general formula VI is one or more of compounds shown in general formulas IV-a to IV-l,
the compound shown in the general formula V is one or more of compounds shown in general formulas V-a-V-e;
the compound shown in the general formula VI is one or more of compounds shown in general formulas VI-a to VI-q,
wherein,
(F) is-H or-F.
4. The liquid crystal composition containing a difluoromethoxy bridge type polar monomer compound as claimed in claim 3, wherein:
the compound shown in the general formula I is one or more compounds shown in general formulas I-a-1-I-r-3,
the compound shown in the general formula II is selected from one or more compounds shown in general formulas II-a-1 to II-r-3,
the compound shown in the general formula III is selected from one or more compounds shown in the general formula III-a-1 to the general formula III-i-3,
the compound shown in the general formula IV is one or more of compounds shown in general formulas IV-a-1 to IV-l-4,
the compound shown in the general formula V is one or more compounds shown in general formulas V-a-1-V-e-3,
the compound shown in the general formula VI is one or more compounds shown in the general formulas VI-a-1 to VI-q-3,
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| CN102964226B (en) * | 2012-12-14 | 2015-04-29 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclobutyl and difluoromethylenedioxy connecting radical as well as preparation method and application thereof |
| CN103351879B (en) * | 2013-07-10 | 2015-04-08 | 石家庄诚志永华显示材料有限公司 | Positive dielectric anisotropic liquid crystal composition |
| CN103468271B (en) * | 2013-09-25 | 2015-05-20 | 石家庄诚志永华显示材料有限公司 | Positive dielectric anisotropy liquid crystal composition |
| CN103484130B (en) * | 2013-09-25 | 2015-05-20 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition containing butyl and alkyl compounds |
| CN105586049B (en) * | 2014-10-20 | 2018-05-04 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN105586053B (en) * | 2014-10-20 | 2018-09-21 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN105586052B (en) * | 2014-10-20 | 2018-03-23 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN105505403B (en) * | 2014-10-20 | 2018-07-24 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its display device |
| CN105505402B (en) * | 2014-10-20 | 2018-03-23 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN105586057B (en) * | 2014-10-20 | 2018-01-30 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN105567254B (en) * | 2014-10-20 | 2018-03-23 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and liquid crystal display device |
| CN105586051B (en) * | 2014-10-20 | 2018-05-04 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN106147793B (en) * | 2015-04-23 | 2018-01-30 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and liquid crystal display device |
| CN106147786B (en) * | 2015-04-23 | 2018-10-30 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its liquid crystal display device |
| CN106147789B (en) * | 2015-04-23 | 2018-01-30 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and liquid crystal display device |
| CN106635056B (en) * | 2015-11-02 | 2018-09-11 | 江苏和成显示科技有限公司 | Liquid-crystal composition and its display device |
| CN106566563B (en) * | 2016-10-26 | 2019-08-16 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition |
| CN106565487B (en) * | 2016-10-26 | 2019-02-26 | 烟台显华化工科技有限公司 | A kind of terphenyl compound and the liquid-crystal composition comprising it |
| CN108587647A (en) * | 2018-06-05 | 2018-09-28 | 晶美晟光电材料（南京）有限公司 | A kind of positive type liquid crystal compound, the liquid crystal compound comprising the liquid-crystal compounds and its application |
| CN112980458B (en) * | 2019-12-13 | 2022-07-22 | 北京八亿时空液晶科技股份有限公司 | Bridged naphthene-containing liquid crystal compound and preparation method and application thereof |
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| DE4239169A1 (en) * | 1992-11-21 | 1994-05-26 | Merck Patent Gmbh | Cyclobutane - benzene derivatives |
| JP2000256228A (en) * | 1999-03-05 | 2000-09-19 | Asahi Denka Kogyo Kk | Alkenylcyclobutane compound |
| JP2006508154A (en) * | 2002-12-02 | 2006-03-09 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Cyclobutane derivative |
| CN102964226B (en) * | 2012-12-14 | 2015-04-29 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclobutyl and difluoromethylenedioxy connecting radical as well as preparation method and application thereof |
| CN103275735B (en) * | 2013-05-13 | 2015-04-08 | 石家庄诚志永华显示材料有限公司 | Dielectric positive liquid crystal composition |
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